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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
La transanalización de los 1-sulfonil-1,2,3-triazoles con los heterocumulenos también es posible
Stepan Chuprakov1, Sen Wai Kwok, Valery V Fokin
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|March 13, 2013
Resumen
Este estudio demuestra una nueva reacción catalizada por Rh (II) que convierte 1-mesil-1,2,3-triazoles en diversas imidazolonas y tiazolas. El proceso implica azavinil reactivo metales-carbenos para la síntesis eficiente de heterociclos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Química Heterocíclica La Química Heterocíclica es una de las más conocidas.
Sus antecedentes:
- Los 1,2,3-triazoles son unos versátiles intermediarios sintéticos.
- El desarrollo de métodos eficientes para la síntesis heterocíclica es crucial en la química medicinal.
- Las reacciones catalizadas por el rodio (II) ofrecen vías únicas para las transformaciones moleculares.
Objetivo del estudio:
- Desarrollar una nueva ruta sintética para las imidazolonas y tiazolas.
- Para explorar la reactividad de los 1-mesil-1,2,3-triazoles en las transformaciones desnitrogenativas.
- Para investigar el mecanismo que involucra a los metales-carbenos de azavinilo.
Principales métodos:
- El rodio (II) en la catálisis.
- Reacciones desnitrogenativas de 1-mesil-1,2,3-triazoles con isocyanatos y isotiocyanatos.
- Estudios mecanicistas que incluyen productos intermedios propuestos.
Principales resultados:
- Conversión eficiente de 1-mesil-1,2,3-triazoles a las imidazolonas y tiazolas.
- Formación de azavinil metal-carbenos a través de un equilibrio de triazol-diazoimina.
- Demostración de la transformación del núcleo del heterociclo.
Conclusiones:
- Un nuevo método catalizado por Rh (II) proporciona acceso a diversas imidazolonas y tiazolas.
- La reacción procede a través de un intermediario propuesto de azavinilo metal-carbeno.
- Esta metodología ofrece una herramienta valiosa para la construcción de andamios heterocíclicos complejos.
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